40+ This or That Questions to Get to Know Someone
Getting to know coworkers does not require sharing secrets — it requires enough small data points that a name becomes a person. This or That questions supply exactly that: one-word answers that, repeated across weeks, assemble a portrait nobody could have extracted from a direct conversation.
These prompts are chosen for colleague-to-colleague comfort. They touch preferences, habits and gentle tastes rather than private life, so answering next to your manager feels as safe as answering next to your work friend. That safety is what makes people answer honestly.
Teams that keep a running rotation discover the compound effect quickly: you stop guessing whether a teammate prefers deep work or open doors, you just know. Every answered binary is one fewer assumption, and assumptions are where friction quietly starts.
40+ This or That Questions to Get to Know Someone
No signup or filters - every item in this collection is on this page: work-safe, copy-ready. The full set of 92 dilemmas.
Preferences(92)
Early bird or Night owl
Beach or Mountains
Podcast or Music
City break or Nature escape
Walk and talk or Sit and focus
Sunrise or Sunset
Books or Movies
Hot weather or Cold weather
One long break or Several short breaks
Always be five minutes early or Never have to rush
Give anonymously or Give where it's seen
Forgive quickly or Talk it through first
Show 80 more dilemmas
Take one day fully off or Leave the phone behind all Sunday
Road trip or Fly
Morning workout or Evening workout
Cook at home or Order in
Cats or Dogs
Texting or Calling
Re-read a favorite or Start something new
Planned itinerary or Wander freely
Big city or Small town
Subtitles on or Subtitles off
Summer or Winter
Vinyl or Streaming
Museum or Concert
Early dinner or Late dinner
Save first or Spend first
Late night out or Early morning start
One month off or Longer weekends
Read the sequel first or Read the original first
Cook a new recipe every week or Master five recipes
Spend on experiences or Spend on things
Weekend marathon or Weekly episode
Window seat or Aisle seat
Slow morning or Fast morning
Batch errands or Errand by errand
Longer vacation or Shorter vacations
Handwritten list or Digital list
Pottery class or Language class
Weekend project or Weekend off
Gift experience or Gift object
Same restaurant every time or Always try a new one
Early flight or Late flight
Window down or Music up
Pack light or Pack everything
Same seat every time or Rotate seats
Gift a book or Gift a plant
Hot shower or Cold plunge
Wander the aisles or Shop with a list
Plants at home or Art at home
Carry a notebook or Keep notes in your phone
Plan every hour or Improvise the day
Same lunch spot or Rotate lunch spots
Reply instantly or Batch replies
Wake before dawn or Work past midnight
Travel carry-on only or Check a big bag
Watch the game live or Read the highlights
Coffee before talk or Talk before coffee
Sort by price or Sort by rating
Long book, deep dive or Short book, quick win
One big trip or Several small trips
Wake up to an alarm or Wake up naturally
Take the stairs or Wait for the elevator
Playlist first or Podcast first
Airplane mode at night or Notifications all night
Sunday reset or Friday reset
Weekday dinner out or Weekend dinner in
Deep clean on Saturday or Tidy a little daily
Second coffee after lunch or Nap instead
Inbox at 9 or Inbox at 5
Music while working or Silence while working
Sit for lunch or Walk for lunch
Same breakfast every day or Mix it up
Voice message or Typed message
Bright screen or Dim screen
Read the agenda or Skip to decisions
Snack at the desk or Snack in the kitchen
reorder the same meal every visit
read the last chapter first
pack three days before the flight
choose the window seat every time
keep the phone face down at dinner
take the longest route home
reread the favorite chapter
queue the next episode instantly
dog-ear every page
brew the coffee before anything else
keep a running list of recommendations
choose the aisle for the stretch
sleep in on both days off
save the fancy place for celebrations
keep the notes handwritten
Frequently asked questions
What should you ask a coworker you do not know well?
Low-stakes preferences with obvious answers: coffee or tea, early or late, screen or silence. Familiar questions produce easy answers, and easy answers create the repeated contact that familiarity is built from.
How do you get to know teammates without awkward personal questions?
Use formats where disclosure is minimal by design — a one-word pick reveals a preference without inviting a life story. The structure itself protects people from oversharing while still generating connection.
Are this or that questions good for new joiners?
They are ideal, because a new teammate can answer day one with zero company context. Early participation in a shared ritual gives the joiner a voice before their first contribution lands in a document.
How often should coworkers swap quick questions?
A few per week in the team channel sustains familiarity without becoming noise. Enough repetition to remember answers, not so much that the exercise starts feeling like a survey.